Bill Callahan has checked off just about every box on the great indie rock scavenger hunt. Ultra-obscure self-released cassettes? Yep. Extra-hissy early lo-fi recordings? Absolutely. Sad-bastard chamber pop albums? He’s done a few, in fact. Alt-country, slowcore, eclectic kitchen-sink pop and, finally, just rock? Yes, yes, yes, and definitely yes. And this is the kicker: It’s almost always great. But that doesn’t mean Callahan isn’t a tough nut to crack for those with no background in Bill.
Callahan — who up until 2007 recorded as Smog — is a bit like indie rock’s version of The Most Interesting Man In the World. He’s nomadic and enigmatic, he’s had a number of relationships with semi-famous women (Chan Marshall, Joanna Newsom, etc.), and his masculine, rugged — yet vulnerable — image tends to go against the grain of North American Indie Rock (unless you’re Matt Berninger, who likely was heavily influenced by Callahan). Callahan can say more in five words than most singers can say in 20, and yet those five words can contain endless layers of meaning. And even 10 years after the fact, people often still dive deep into the subtext of Callahan’s evocative poetry. And we’ll get to that shortly.
Bill Callahan has been releasing music since the late ’80s, and in that time he’s released 11 studio albums as Smog, four under his own name, plus a long list of EPs, singles, cassettes and other ephemera — almost all on Drag City. That’s a lot to dive into, and for a songwriter as prolific and eclectic as he is, it can be hard to know where exactly to start listening. We’ve spent some quality time with his music, so if you’re ready to take the journey, follow us on our beginners guide, starting with five of the best Bill Callahan albums—as well as the most accessible—and where to go next.
(1998; Drag City)
Where does one begin with the ample, overwhelming catalog of Bill Callahan? That’s a tough one to answer in a way that works for everyone. Some might suggest you work from the top, going from his earliest lo-fi experimentation and easing into his later, earthier material. Others might suggest working backwards, getting a feel for Callahan the rugged elder statesman before hearing how he collaborates with tape hiss. And then there’s the idea of just picking his most acclaimed album (which is probably 1997’s Red Apple Falls) and spiraling outward. But there’s a much easier — dare I say it? — correct answer. You start with Knock Knock.
Surveying Callahan’s career as a whole, no record of his better fits at the center of his complicated, sometimes contradictory musical universe than this 1998 record, a perfect bridge between his four-track and drum-machine beginnings and the full-band sound he’s since sharpened and damn near perfected. For all intents and purposes, Knock Knock is a full band album, a plentiful chunk of its songs fleshed out with drums, bass, piano and plenty of guitar effects. Callahan rocks out pretty regularly — on “Held,” on the grungy “No Dancing,” and on the undeniably catchy “Cold Blooded Old Times.” There are moments of arrestingly gentle grace as well — “Teenage Spaceship” is breathtaking — but that’s not really so surprising. Bill letting out a hearty “Woo!” as “Held” kicks into high gear? That was a bit more unexpected at the time — and seeing as how this is the first Bill Callahan album I’m telling you to listen to, you can go ahead and mark that one down as a pleasant surprise.
None of the fun little production flourishes or hard-rocking vibes employed on Knock Knock serve to undermine Callahan’s enigmatic and emotionally charged poetry, however. As ripe for hand-clapping and sing-alongs as “Cold Blooded Old Times” is, it’s scarred from trauma and abuse: “How can I stand, and laugh with the man/ who redefined your body?” And on “Held,” Callahan opens himself up to expose a vulnerable side that might initially seem at odds with the masculine image and voice he’s known for: “For the first time in my life/ I let myself be held/ like a big old baby.” Really, it’s not hard to let Knock Knock break your heart. It almost certainly will, in fact. But it could just as easily have you dancing or singing along, and an album that can pull off all of this at once is a powerful one indeed.
Listen: Smog – “Cold Blooded Old Times”
(2011; Drag City)
After Callahan dropped his Smog moniker in 2007 with the release of Woke On a Whaleheart, it wasn’t long before he ended up recording his most accessible album yet: 2009’s Sometimes I Wish We Were An Eagle. It’s a lush, warm record, featuring very little in common with any of his early recordings as Smog. And that was sort of the point of the shift, it seemed: There was no longer any need to use a different name. Callahan had already traveled so far a distance from his early lo-fi sounds that he ended up somewhere he could breathe more easily, with spacious and open skies.
But that doesn’t mean he didn’t still obscure his message, or enjoy just getting weird. His third album under his own name, Apocalypse, is a bit less straightforward than Sometimes I Wish We Were An Eagle, but there’s an electricity and vibrancy about it that makes it a lot of fun to listen to. In its opening track, “Drover,” Callahan strums a progression of two harsh and percussive chords, which at first might bring to mind “Avalanche,” the opening track from Leonard Cohen’s Songs of Love and Hate. Soon enough and that transforms into a lightning storm of a western song, with heavily reverbed electric guitar and rugged, ragged narration. He puts extra emphasis on the “Wild, wild country” he describes, which seemingly puts him at odds with the outside world: “I set my watch to the city clock/ It was way off!”
Callahan is both invested in and alienated by his detachment from other people — often through character sketches — but for such an insular album, Apocalypse feels pretty exciting at times, as on the rapidly shifting tempos on “Baby’s Breath,” or the loose jam of “America!”, which pretty much rocks. Apocalypse was recorded with a live band, so, you know, having a group of people playing rock music in the same room will do that. But then, Apocalypse also contains “Riding For the Feeling,” one of the most serene and beautiful songs in Callahan’s catalog, so it’s not all bashing away. It is Callahan sounding his most natural and live, though, and even if it doesn’t click immediately, just give it a little longer. It will.
Listen: Bill Callahan – “America!”
Red Apple Falls
(1997; Drag City)
As Bill Callahan has matured as a songwriter, he’s fairly successfully shaken the sad-bastard stereotype that hung around during most of his Smog years. Not that he didn’t earn that badge in his day, but if Callahan indeed was a sad bastard, he was one of an elite group of such singer/songwriters, like Elliott Smith and Mark Kozelek, who made melancholy into a higher form of art. He just about perfected it on 1997’s Red Apple Falls, a lushly arranged, gently performed set of indie-folk and chamber-pop heartbreakers.
The thing is, Red Apple Falls is actually where Callahan begins to let more light into his chamber, allowing his songs of comedy and tragedy to leave a heavier impact without seeming quite as heavy, thematically. There’s sadness here, certainly, which manifests in seemingly connected narratives about relationships — or one in particular — all of which are given gorgeously rich backings, thanks in large part to producer Jim O’Rourke. Standout “I Am A Stranger” is one of the strongest tracks here, its sound shimmering with weepy lap steel and some of Callahan’s most affecting lyrics: “You should have seen what I was in the last town/Or in the last town/I was worse than a stranger/I was well known.” The meditative ambient pop of the title track finds him following a man made of onions who “knows the way.” And the upbeat “Ex-Con” breaks up the slower, spacious tracks with a one-chord piano hook and wobbly-sounding horns, and a whole notebook’s worth of notable quotables: “Whenever I get dressed up/ I feel like an ex-con trying to make good,” “Alone in my room, I feel like such a part of the community/ But out on the streets, I feel like a robot by the river,” et al. Oh, and “Inspirational”? We can just go ahead and say that’s an aptly named tune if there ever was one.
On Red Apple Falls, Callahan is still sad, still hilarious, still a mystery. Not that any of that would change, really, just concentrated in different ratios. Here, it’s all perfectly balanced — everything that Callahan is capable of in a beautiful and concise package.
Listen: Smog – “Red Apples”
(2013; Drag City)
In his review of the album last year, Treble’s Tyler Parks suggested that his favorite of Callahan’s records was Apocalypse — until Dream River came along. There’s an inherent reticence among most of us to champion a new album over something we’ve had a lot more time to live with, but Dream River is such a strong and overwhelming statement, even without the history of an album like Knock Knock, or even Sometimes I Wish We Were An Eagle, it feels like an incredible achievement. It’s a sensorial experience, from its most hushed moments (“Small Plane”) to its stormiest (“Summer Painter”), and it’s the latter that crop up a little more often — not something that’s often said of Callahan’s albums.
Dream River is also one of Callahan’s darkest albums. It’s not so much sad or troubled as it is outright ominous. On “Spring,” he sings, “They call it spring, though things are dying/ Connected to the land, like a severed hand.” And the mesmerizing “Summer Painter” has an arrangement to mirror its narration, with the music growing gradually more intense as Callahan describes a hurricane barreling into town — a hurricane he was lucky enough to miss. The ways in which the music and lyrics are intertwined on Dream River display a sophistication and attention to detail that only come from a true master of his craft. Not that any of Callahan’s wit or charm has been lost in this tempest of an album — more apocalyptic than Apocalypse. In the more unassuming opener, “The Sing,” Callahan delivers a lyric that’s both genius in its simplicity, and entirely representative of his whole essence: “The only words I’ve said today are ‘beer’ and ‘thank you’/ Beer/ Thank you.”
Listen: Bill Callahan – “Summer Painter”
Dongs of Sevotion
(2000; Drag City)
If you need just one reason to listen to Dongs of Sevotion, I’ll give you an easy one: “Dress Sexy At My Funeral.” The second track on the album — following the rich, densely arranged opener “Justice Aversion” — it’s essentially everything that Bill Callahan does better than anyone else in a five-minute, 30-second package. It’s a top-five Callahan contender, intertwining wry humor, romance and caricaturistic hubris into a surprisingly affecting folk-rock tune. There’s a catchy hook to it (“Dress sexy at my funeral, my good wife”) and an almost tragic need to be recognized for his triumphs and good deeds, perceived or imaginary (“Tell them about the time we did it/ On the beach with the fireworks above us … Also tell them about how I gave to charity/ And loved my fellow man, as best I could/ But most of all don’t forget about the time on the beach”). “Dress Sexy at My Funeral” is a perfect song. Actually, it might even be better than that.
It’s, of course, not the only reason to listen to Dongs of Sevotion. There are 10 more, which are quite near that impeccable peak, running a wide stylistic range from the eerie and mournful “Nineteen” to the grungy “The Hard Road,” with interesting curiosities like “Bloodflow” in between, with both rich sonic textures and a cheerleader chant about machetes. Dongs of Sevotion is one of Callahan’s longer albums, and takes a bit of patience — though not to the extent of a quieter album like Rain on Lens — but it’s also one that yields some powerful rewards with each new spin. And I’d be remiss not to mention the title, which takes an earnest, romantic concept and spoonerizes it into a dick joke. That Bill.
Also Recommended: Without a doubt, 2009’s Sometimes I Wish We Were An Eagle deserves a place here, even though we’re still sticking with the arbitrary cut-off of five albums per Beginner’s Guide. It’s an essential next step, however. Likewise, 1996’s The Doctor Came At Dawn is an excellent transition into more ambitious (and still sad) territory for Callahan, while 2005’s A River Ain’t Too Much To Love is another set of lovely tunes, and serves — both chronologically and stylistically — as a proper bridge between his work as Smog and that which bears his own name. Plus 2019’s Gold Record shows that growing more domestic hasn’t dulled his edge in the slightest.
Advanced Listening: You don’t really get a good idea of what Bill Callahan is all about with his newly released “dub” album, Have Fun With God. But that’s not a bad listen for those a bit more curious. Before that, however, I’d suggest a dive into his earlier lo-fi Smog records, in particular 1993’s Julius Caesar and 1995’s Wild Love. The former is a bit less accessible than the latter, though both are early sketches full of tape hiss, homespun charm and flashes of general weirdness. He still manages to do a bang-up job, it turns out.
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Jeff Terich is the founder and editor of Treble. He's been writing about music for 20 years and has been published at American Songwriter, Bandcamp Daily, Reverb, Spin, Stereogum, uDiscoverMusic, VinylMePlease and some others that he's forgetting right now. He's still not tired of it.